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512931

Sigma-Aldrich

3,4-(Methylenedioxy)phenylmagnesium bromide solution

1.0 M in THF: toluene (1:1)

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About This Item

Empirical Formula (Hill Notation):
C7H5BrMgO2
CAS Number:
17680-04-5
Molecular Weight:
225.32
MDL number:
MFCD01863705
UNSPSC Code:
12352103
PubChem Substance ID:
24873661
NACRES:
NA.22

reaction suitability

reaction type: Grignard Reaction

concentration

1.0 M in THF: toluene (1:1)

density

1.04 g/mL at 25 °C

SMILES string

Br[Mg]c1ccc2OCOc2c1

InChI

1S/C7H5O2.BrH.Mg/c1-2-4-7-6(3-1)8-5-9-7;;/h1,3-4H,5H2;1H;/q;;+1/p-1

InChI key

JFUHZUGUHBLMLB-UHFFFAOYSA-M

Application

3,4-(Methylenedioxy)phenylmagnesium bromide can be used as a reagent in the total synthesis of (+ )-paulownin from the starting material (R)-( + )-3-hydroxybutanolide. It is also used in the total synthesis of (+)-vittatine , and (+)-magnostellin C.

signalword

Danger

Hazard Classifications

Aquatic Chronic 3 - Asp. Tox. 1 - Carc. 2 - Eye Dam. 1 - Flam. Liq. 2 - Repr. 2 - Skin Corr. 1B - STOT RE 2 - STOT SE 3

target_organs

Central nervous system, Respiratory system

Storage Class

4.3 - Hazardous materials which set free flammable gases upon contact with water

wgk_germany

WGK 3

flash_point_f

14.0 °F - closed cup

flash_point_c

-10 °C - closed cup

Certificates of Analysis (COA)

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First stereoselective synthesis of (+)-magnostellin C, a tetrahydrofuran type of lignan bearing a chiral secondary benzyl alcohol
Yamauchi, Satoshi and Kinoshita, Yoshiro
Bioscience, Biotechnology, and Biochemistry, 65(7), 1559-1567 (2001)
Total synthesis of (+)-paulownin
Okazaki M, et al.
Bioscience, Biotechnology, and Biochemistry, 61(4), 743-745 (1997)
Masahiro Bohno et al.
Chemical communications (Cambridge, England), (9), 1086-1087 (2004-04-30)
The stereoselective and chiral synthesis of the Amaryllidaceae alkaloid, (+)-vittatine 1, is described; the quaternary carbon in 1 was generated by Claisen rearrangement of a cyclohexenol derived from D-glucose by way of a Ferrier's carbocyclisation reaction and a hexahydroindole skeleton

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